(2,4-Dichlorophenyl)boronic acid → HCID 86679887, compound

HRID 1519397Notes

Reaction equation

HRID 1519397 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)[CH:7]=[CH:6][C:5]=1Br.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:5]1[C:4]([C:3]([OH:2])=[O:24])=[CH:9][C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679887HCID 86679887, compoundYield 65.6%

Procedure

Using the conditions of General Procedure B for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 89 mg, 0.2 mmol) was reacted with 2,4-dichlorophenylboronic acid (available from Combi-Blocks Inc.; 76 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′,4′-dichloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (65 mg, 65%). 1H NMR (400 MHz, DMSO-d6) δ 13.15 (br s, 1H), 8.55 (s, 1H), 8.49 (s, 1H), 8.34 (s, 1H), 8.29 (d, J=7.8 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.78 (d, J=8.3 Hz, 1H), 7.70 (s, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.36-7.43 (m, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-8e6d91c02b0642f19aad8d9f3c3ef75f
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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